Schmidt, who is stepping down as Alphabet’s chairman, has a history of shining boardroom achievements (and clumsy public statements).

Eric Schmidt, who stepped down Thursday as Alphabet’s chairman, is one of the most influential tech executives in history–and among the wealthiest–but he’s also among the most awkward where public relations is concerned.

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Google’s financial results since Schmidt was brought in in 2001 to help guide the youngish company’s business strategy are obvious—the stock is currently trading at over $1,070 a share. This timeline marks out the big items in Schmidt’s bio, before and after Google, and sprinkles in some of the public missteps he’s made over the years.

April 1997 to November 2001 — Takes over as CEO, then chairman at Novell Inc.

March 2001 — Recruited by Larry Page and Sergey Brin, and joins Google as chairman of the board, where he served until April 2004, and then again from April 2007 to April 3, 2011. He was CEO from August 2001 until April 2011.

August 2005 — Google blackballedCNet for a year after the publication ran a story including some sensitive details about Schmidt’s residence, political persuasion, and paycheck. Elinor Mills, the CNet reporter, used Google’s search engine to find it all.

August 29, 2006, to July 31, 2009 — Serves as a board member at Apple, then steps down when Apple and Google begin to seem more like competitors than friends.

August 2010 — Schmidt tells the Wall Street Journal he believes every young person will one day be allowed to change their name to distance themselves from embarrassing photographs and material stored on their friends’ social media sites.

September 7, 2010 — “We can suggest what you should do next, what you care about. Imagine: We know where you are, we know what you like,” Schmidt said as the IFA’s keynote speech in Berlin, amping up the creepiness.

September 22, 2010 — “It’s true that we see your searches. But we forget them after a while,” Schmidt said during a The Colbert Report segment, when the jocular host asked Schmidt to confirm whether Google knows all “our likes [and] dislikes.”

October 2010 — Schmidt, talking to The Hill about privacy issues, says Google gets “right up to the creepy line.”

April 2011 — Schmidt steps down as CEO of Google, handing the reins to Larry Page. Schmidt had taken just $1 a year in salary since 2004, but on his departure as CEO Google gave him a big fat $100 million reward in cash and stock options.

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April 2014 — Google, Apple, Adobe, and Intel agree to settle tech employees’ class action suit claiming the companies had agreed not to poach each other’s employees (therefore holding down salaries). Schmidt is given much of the credit for initiating a “do not call” list of employees the companies agreed not to recruit.

August 2015 — Google announces it’s created an umbrella organization called Alphabet, under which Google and all its “other bets” companies will function. Schmidt became Alphabet’s executive chairman. With others acting as CEOs over the various Alphabet companies, Schmidt’s role concerned high-level strategic vision and dealings with governments domestic and foreign.